With discussions revolving around the historic significance of the Kings Highway bridge on the old Post Road, the question of how old the road really is has been raised.

The Boston Post Road was a system of mail-delivery routes between New York City and Boston that evolved into one of the first major highways in the United States.

The three major alignments were the Lower Post Road (now U.S. Route 1) along the shore via Providence, R.I. , the Upper Post Road (now U.S. 5 and U.S. 20 from New Haven by way of Springfield, Mass.), and the Middle Post Road (which diverged from the Upper Road in Hartford and ran northeastward to Boston via Pomfret).

The Upper Post Road was originally called the Pequot Path and had been in use by Native Americans long before Europeans arrived. Some of these important native trails were in many places as narrow as two feet.

What is now called Old Connecticut Path and Bay Path were used by John Winthrop the younger to travel from Boston to Springfield in November, 1645, and these form much of the basis for the Upper Post Road.

The colonists first used this trail to deliver the mail using post riders. The first ride to lay out the Upper Post Road started on January 1, 1673. Later, the newly blazed trail was widened and smoothed to the point where horse-drawn wagons or stagecoaches could use the road. The country’s first successful long-distance stagecoach service was launched by Levi Pease along the upper road in October 1783.